2-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chloride → 2-(2,4-Bis(tert-pentyl)phenoxy)-N-(3,5-dichloro-4-ethyl-2-hydroxyphenyl)butyramide

HRID 1635696Notes

Reaction equation

HRID 1635696 reaction equation
C(=O)(O)[O-].[K+].[Cl:6][C:7]1[C:8]([OH:17])=[C:9]([CH:11]=[C:12]([Cl:16])[C:13]=1[CH2:14][CH3:15])[NH2:10].[CH3:18][C:19]([C:23]1[CH:35]=[C:34]([C:36]([CH3:40])([CH3:39])[CH2:37][CH3:38])[CH:33]=[CH:32][C:24]=1[O:25][CH:26]([CH2:30][CH3:31])[C:27](Cl)=[O:28])([CH3:22])[CH2:20][CH3:21]>C(O)(C)C.O.C1(C)C=CC=CC=1.CCCCCCC>[CH3:22][C:19]([C:23]1[CH:35]=[C:34]([C:36]([CH3:39])([CH3:40])[CH2:37][CH3:38])[CH:33]=[CH:32][C:24]=1[O:25][CH:26]([CH2:30][CH3:31])[C:27]([NH:10][C:9]1[CH:11]=[C:12]([Cl:16])[C:13]([CH2:14][CH3:15])=[C:7]([Cl:6])[C:8]=1[OH:17])=[O:28])([CH3:18])[CH2:20][CH3:21]

Participants

8

Reactant 3

HCID 1703932-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chlorideHCID 516893Potassium Bicarbonate3×HCID 117696522,4-Dichloro-3-ethyl-6-aminophenol

Product 1

HCID 1755692-(2,4-Bis(tert-pentyl)phenoxy)-N-(3,5-dichloro-4-ethyl-2-hydroxyphenyl)butyramide

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×HCID 3776IsopropanolSolvent2×HCID 8900HeptaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A heel was created via batch mode in Reactor 1 by first adding of 16 g (0.16 moles) of potassium bicarbonate, and 55 g of deionized water, and stirring until all of the solid had dissolved. Then, 24 g of isopropanol, 30 g (0.146 moles) of 3,5-dichloro-4-ethyl-2-hydroxyaniline (the amine), 120 g of heptane, and 20 g of toluene were added. The contents of the reactor system were heated to approximately 60° C. while agitating at 400 rpm. To this 2-phase mixture, 57.5 g (0.169 moles) of 2-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyryl chloride (the acid chloride) were added over approximately 45 minutes. The analysis of the upper phase of the mixture was 94% product on a solvent free-basis. The continuous feeds were started at the following rates to provide six hours of residence time: 0.51 g/min 1.36 mmoles/min) of a 55 wt % solution of amine in isopropanol; 1.82 g/min (1.48 mmoles/min) of a solution of the acid chloride solution (27.5 wt % in a mixture of 6 parts of heptane and 1 part of toluene. A 22.5 wt % solution of potassium bicarbonate in water was added to maintain the pH between about 2 and 4. The flowrate of the potassium bicarbonate solution ranged from 0.64-0.68 g/min (1.37-1.46 mmoles/minute).

Workup

  1. customA heel was created via batch mode in Reactor
  2. dissolutionhad dissolved
  3. stirringwhile agitating at 400 rpm
  4. customto provide six hours of residence time
  5. temperatureto maintain the pH between about 2 and 4

Sources & evidence

ORD record
ord-9e6036ccb79d47f597947b2fda761384
Source dataset
uspto-grants-2003_01
Patent number
US06509500B2

Reaction notes

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